


Hard Day’s Night

by DRHPaints



Category: Conan O’Brien, Conan O’Brien RPF, Late Night Host RPF
Genre: Angry Sex, Biting, Conan O’Brien - Freeform, Dirty Talk, Established Relationship, Explicit Language, Explicit Sexual Content, F/M, Face Slapping, Masturbation, One Shot, Phone Sex, Rough Sex, Smut, Spanking, Vaginal Fingering
Language: English
Status: Completed
Published: 2020-08-07
Updated: 2020-08-07
Packaged: 2021-03-06 08:00:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,036
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25760011
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Conan has a rough day at the office, and even though Gwendolyn helps him out over the phone while he’s stuck there, he still has a lot of anger to work through by the time he gets home.
Relationships: Conan O’Brien/Original Female Character
Comments: 4
Kudos: 9





	Hard Day’s Night

Running his hands over his face, Conan sighed. He looked at the clock.  _ Only one? What the hell… _ It had been a miserably long day already. Staff meetings, a ‘gentle heads up’ from his producer Jeff Ross that a joke from last night’s monologue had rubbed folks the wrong way and was starting a small firestorm on Twitter, and to top it off, ratings were down. 

Puffing out his cheeks and letting out a slow exhale, Conan picked up his phone to text Gwendolyn. She could usually cheer him up on a hard day.

_ Hey, how’s it going? _ __

Looking at his screen expectantly, Conan grinned when he saw the dots begin to dance.

Gwendolyn:  _ Oh, not too bad. Just out shopping. You? _

__ Conan:  _ Rough day. Lots of headaches. Wish I was home with you. _

It was a few moments before she responded, and when she did, Conan noticed there was a picture attached.

Gwendolyn:  _ I’ll be ready and waiting… _

Opening the attachment, he saw Gwendolyn standing in a dressing room, head turned to the side and smiling coyly, crimson hair a tumble as she held her phone up to the mirror, wearing nothing but a black thong, one arm draped across her breasts, barely covering them.

“Oh  _ fuck. _ ” Conan whispered to himself, thumbs flying over the keyboard.

Conan:  _ You can’t do this to me, ha. I’m stuck here for at least five more hours. _

__ Gwendolyn still hadn’t responded after a couple of minutes, so Conan set his phone aside and returned to his paperwork. About 20 minutes later it vibrated on his desk.

Gwendolyn:  _ Sorry, I was checking out and driving. Alone at home in bed now, thinking of you. Are you free to call? _

__ Smirking, Conan pushed back from his desk and scurried to the door. Peeking out, he saw that Sona was away, and closing and locking it, he returned to his chair. 

Dialing, Gwendolyn picked up almost immediately. “Hey there.” Her voice was low, sultry, and it made the hair on the back of Conan’s neck stand up as he leaned back.

“Hey,” he responded. Conan never liked the sound of his own voice, despite Gwendolyn telling him she found it ‘sexy.’ At the same time, he had to admit dirty talk lit a spark in him, so he did his best to look past it.

“So you’re having a hard day?” Gwendolyn asked.

Conan nodded, even though he knew she couldn’t see him. “Yeah.”

“Mmm…” she let out a long, deep hum that reverberated straight down to his cock. “Maybe you should take it out on me then…”

Swallowing, Conan’s tongue flashed over his lips. “Yeah? What do you want me to do?”

“Oh, I don’t know…” he heard her inhale. “Maybe you could hold me down on the bed.”

“Mmhmm, yeah. What else?” Sliding a hand down, Conan began palming his hardening cock through his jeans.

“And you lay on top of me and start grinding that big, hard cock against my wet pussy.” Gwendolyn spoke each word deliberately, letting them drip from her mouth, and Conan could picture her voluptuous lips forming every syllable.

Unzipping his jeans, Conan took himself in hand. “Yeah, you like that, don’t you? You like when I rub my cock up against you.”

“I love it.” She breathed. “You feel so fucking good, Conan.”

Stroking, Conan took a deep breath. “Yeah, now I’m sliding my hand in between your legs.”

“Fuck, Conan, you’re making me so wet.” Gwendolyn panted.

Hand speeding up around his cock, Conan swallowed. “Yeah, you love it when I rub your clit, don’t you? You go crazy when I’m fucking you with my fingers.”

“Yeah, Conan, fuck. Put them inside me, I love your big hands.” Gwendolyn whined. “Fuck, Let me touch you, Conan. I wanna feel your big cock.”

Lowering his voice almost impossibly deeper, Conan smirked. “Yeah? I’ll let one of your hands go so you can stroke me I guess.” Gwendolyn let out a tiny moan and Conan rubbed his thumb over the head of his cock, squeezing gently. 

“Mmm...yeah, I love your cock. You’re so fucking thick. Are you hard for me, Conan?”

Panting, Conan pressed the phone to his ear. “Fuck yeah, so hard for you Gwen.” He began thrusting up into the warm circle of his fist. “Let me fuck you, Gwen. I wanna fuck you so badly.”

Gwendolyn let out a mewling whine and Conan had to bite his lip to restrain himself from rushing to the finish line. “Yeah, fuck me, Conan. I want you inside of me. Fuck me  _ hard _ .”

“I’m inside you. I’m fucking you and you feel so good, Gwen.” Conan gasped, listening to her moans rise in pitch..

“Fuck, Conan, _fuck_ _you’re gonna make me cum_ ,” Gwendolyn whimpered.

Cradling the phone between his ear and his shoulder, Conan grabbed the box of tissue on the corner of his desk, snatching a handful. “Cum for me. Cum for me, Gwen. I fucking love making you cum.”

“ _ Yes, Conan, yes! _ ” She cried, and Conan heard her voice fade and rise as he assumed the phone fell beside her on the pillow. The sounds of her ecstasy were too much, and Conan tugged frantically.

“ _ Oh Gwen, oh fuck,”  _ he groaned, attempting to keep the phone against his ear as he shot into the Kleenex, mouth agape, eyes scrunched tight, rocking in his desk chair. 

Both of their breathing slowly returned to normal as they listened to one another over the phone. “Damn, I want to come home and fuck you for real.” 

Gwendolyn chuckled. “I can’t wait.” Shaking his head, Conan smiled and they made their goodbyes.

The rest of his day...did not go well. In addition to the already mounting hassle, Jeff informed him that one of his best writers quit abruptly, storming off in a huff after complaining of censorship. Filming was rocky, the interview being an uphill battle as Conan couldn’t tell whether the actress was mildly drunk or high, and had to keep prompting her on the questions. Thanking his editors in advance for however they would manage to piece together that shitshow, Conan finally climbed into his Tesla, exhaling and heading home, only to get cut off in traffic by some jackass with a huge spoiler on the back of his shitty compact, who then gave  _ him _ the finger.

By the time he walked through the front door, Conan was boiling. He considered himself an amiable person. Sure, he could be a playful jerk to his friends, and coworkers he was close with, but it was rare that he truly lost his temper. But something inside him wanted to rage.

“Hey honey, your day get any better?” Gwendolyn came padding in wearing a t-shirt and shorts, scarlet hair piled loosely on top of her head. Conan stared at her, eyes ablaze, teeth gritted, hands clenched at his side.

Gwendolyn narrowed her eyes at him. “Conan…?” He began to approach her, expression unchanging. She’d never been in the presence of a feral animal, but she imagined it felt much like this, that silent wariness that you were being pursued, and that one wrong move could prove detrimental. Gwendolyn found herself unconsciously spreading her legs and arms, lowering her body slightly as if readying for attack.

Picking up speed as he grew near, Gwendolyn’s eyes went wide as Conan collided, arms snapping around her and mashing their mouths together, slamming her back against the wall. Gwendolyn squeaked against him in response, but Conan just placed two large hands under her ass, lifting and forcefully grinding his hips into her, erection already evident through his jeans. Burying her hands in his orange hair, Gwendolyn fought to keep up with his mouth, but it was as if Conan was trying to inhale her, breaking away to kiss her neck. Then he bit down on the spot where her neck joined her shoulder.  _ Hard. _

“ _ Conan! _ ” She gasped in surprise. 

Leaning back, Conan looked at her, fiery-eyed as he brought one sizable thumb to the hollow of her throat and growled. “ _ What?” _

Gazing back at him, she studied the hard, flat line of his mouth, saw the way his breath stuttered and felt the pounding of his pulse through the thumb at her throat. Gwendolyn swallowed. “ _ Again. _ ”

Conan took the collar of her t-shirt in both hands and sharply tore it apart, exposing her before swooping down to bite high on her left breast. Letting out a small shriek, Gwendolyn cradled Conan’s head and ground her hips against him as he hooked an arm under her and carried her to the bedroom. 

Throwing her down on the bed, Conan peeled off his t-shirt and shrugged out of his jeans while Gwendolyn discarded her ruined t-shirt, never looking away from his icy blue eyes. 

Pouncing, Conan climbed on top of her, dragging both arms above her head and claiming them in between the fingers of one big hand. Snatching the fabric of her shorts, Conan ripped them away, Gwendolyn writhing underneath him as he reached down and unceremoniously slid his long index and middle fingers inside of her, thumb rubbing her clit.

“ _ Fuck! _ ” She cried, as Conan angled his arm down and began to fuck her with his hand, pulsing into her roughly as his thumb spun. Gwendolyn dug her heels into the mattress, pelvis undulating against his wrist as she moaned.

Beginning to flutter around his fingertips, Conan saw Gwendolyn’s eyes fall shut. “ _ Fuck, Conan, I’m gonna cum.” _

Before Gwendolyn was even aware he’d retracted his hand, it flashed across her face, slapping her and leaving streaks of her wetness across her cheek. 

“ _ You cum when I fucking tell you to _ .” Conan narrowed his eyes and Gwendolyn nodded feverishly, desperate for him to touch her again. 

Still holding her hands tight, Conan rolled on top of her and Gwendolyn groaned at his glorious weight on top of her, as well as the brief brush of his hard cock between her legs. 

“ _ You want me to fuck you? _ ” Conan looked back and forth between Gwendolyn’s viridescent eyes, hand delicately circling her throat.

Rutting her hips against him, she nodded. “ _ Yes. Fuck me. Fuck me, please. _ ”

Conan brought his face millimeters from hers, glaring. “ _ You want me to fuck you hard? _ ”

“ _ Fuck me so hard, Conan. Please, please! _ ” Gwendolyn knew she was begging, but at this point she was beyond caring.

Releasing her hands for a moment, Conan lifted both of her legs over his shoulders and entered her with his massive cock. When Gwendolyn’s hands reached up to trail through his orange hair, he once again pinned them behind her head.

“ _ No. _ ” Conan said firmly as he began hammering into her. Ankles crossed behind his neck, Gwendolyn’s moans turned to screams as every shockingly deep stroke hit home.

“ _ Conan, I can’t...I’m gonna cum. _ ” Gwendolyn cried, and convulsing below him, her body shook uncontrollably, arms straining against his fingers and calves knocking alongside his head as Conan felt her constrict around his cock.

Seeing Gwendolyn was dazed, a wide palm spanked her ass and her eyes flipped open to meet Conan’s. He continued pounding, hips smacking against her viciously as she looked up at his grimacing face. Conan’s clenched teeth highlighted his sharp jawline and his nose was flared, mouth practically a snarl. But it was the eyes... Wild and irregular, they looked like an oncoming storm over the ocean as Conan rocketed into Gwendolyn recklessly. 

Growing close, Conan cupped the back of her head, nails digging into her scalp as he came with a tremendous groan, holding her forehead to his before shuddering on top of her and collapsing.

Catching his breath a little, Conan pressed his thin lips to hers, loosening his grip on her hands and shifting her legs down to his waist, staying inside Gwendolyn as their tongues wound together, hands traveling over her pink-flushed flesh before pulling away to brush a kiss over her chin.

“Was that alright?” Conan pushed her sweaty hair away from her face.

Gwendolyn nodded. “Yeah, yeah, that was fun. I don’t think I’ve ever seen you so...riled up.”

Shrugging, Conan grinned. “Guess that’s what happens when I have a hard day.”

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this, please leave a comment or come say hi on Tumblr at fandomtransmandom :-)


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